CA1303037C - Purinone derivatives as bronchodilators vasodilators and anti-allergic agents - Google Patents
Purinone derivatives as bronchodilators vasodilators and anti-allergic agentsInfo
- Publication number
- CA1303037C CA1303037C CA000557327A CA557327A CA1303037C CA 1303037 C CA1303037 C CA 1303037C CA 000557327 A CA000557327 A CA 000557327A CA 557327 A CA557327 A CA 557327A CA 1303037 C CA1303037 C CA 1303037C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- compounds
- compound according
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
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- 229940124549 vasodilator Drugs 0.000 title claims abstract description 8
- 239000003071 vasodilator agent Substances 0.000 title claims abstract description 8
- 239000000168 bronchodilator agent Substances 0.000 title abstract description 6
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- 239000000043 antiallergic agent Substances 0.000 title abstract description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
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- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims description 11
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878702300A GB8702300D0 (en) | 1987-02-02 | 1987-02-02 | Chemical compounds |
| GB878702301A GB8702301D0 (en) | 1987-02-02 | 1987-02-02 | Chemical compounds |
| GB8702300 | 1987-02-02 | ||
| GB8702301 | 1987-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1303037C true CA1303037C (en) | 1992-06-09 |
Family
ID=26291861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000557327A Expired - Fee Related CA1303037C (en) | 1987-02-02 | 1988-01-26 | Purinone derivatives as bronchodilators vasodilators and anti-allergic agents |
Country Status (10)
Families Citing this family (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8809481D0 (en) * | 1988-04-21 | 1988-05-25 | Smith Kline French Lab | Chemical compounds |
| GB8814352D0 (en) * | 1988-06-16 | 1988-07-20 | Smith Kline French Lab | Chemical compounds |
| US5075310A (en) * | 1988-07-01 | 1991-12-24 | Smith Kline & French Laboratories, Ltd. | Pyrimidone derivatives as bronchodilators |
| GB8817651D0 (en) * | 1988-07-25 | 1988-09-01 | Smith Kline French Lab | Chemical compounds |
| US5250534A (en) * | 1990-06-20 | 1993-10-05 | Pfizer Inc. | Pyrazolopyrimidinone antianginal agents |
| GB9114760D0 (en) * | 1991-07-09 | 1991-08-28 | Pfizer Ltd | Therapeutic agents |
| US5734053A (en) * | 1992-06-26 | 1998-03-31 | Pfizer Inc | Purinone antianginal agents |
| GB9213623D0 (en) * | 1992-06-26 | 1992-08-12 | Pfizer Ltd | Therapeutic agents |
| FI951367A7 (fi) * | 1994-03-28 | 1995-09-29 | Japan Energy Corp | Puriinijohdannaiset ja tulehdustautien tukahduttajat (suppressantit) |
| US5776962A (en) * | 1994-08-03 | 1998-07-07 | Cell Pathways, Inc. | Lactone compounds for treating patient with precancerous lesions |
| US5696159A (en) * | 1994-08-03 | 1997-12-09 | Cell Pathways, Inc. | Lactone compounds for treating patients with precancerous lesions |
| GB9423910D0 (en) * | 1994-11-26 | 1995-01-11 | Pfizer Ltd | Therapeutic agents |
| DE19501480A1 (de) * | 1995-01-19 | 1996-07-25 | Bayer Ag | 9-substituierte 2-(2-n-Alkoxyphenyl)-purin-6-one |
| US6232312B1 (en) | 1995-06-07 | 2001-05-15 | Cell Pathways, Inc. | Method for treating patient having precancerous lesions with a combination of pyrimidopyrimidine derivatives and esters and amides of substituted indenyl acetic acides |
| US6046206A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
| US6060477A (en) * | 1995-06-07 | 2000-05-09 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl cycloamino pyrimidinone derivatives |
| US6046216A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyridinone derivatives |
| US5874440A (en) * | 1995-06-07 | 1999-02-23 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyrimidinone derivatives |
| US6200980B1 (en) | 1995-06-07 | 2001-03-13 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl purinone derivatives |
| US6262059B1 (en) | 1995-06-07 | 2001-07-17 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with quinazoline derivatives |
| CA2238283C (en) * | 1997-05-30 | 2002-08-20 | Cell Pathways, Inc. | Method for identifying compounds for inhibition of neoplastic lesions, pharmaceutical compositions from such compounds and uses of such compounds and compositions for treating neoplastic lesions |
| US5858694A (en) * | 1997-05-30 | 1999-01-12 | Cell Pathways, Inc. | Method for identifying compounds for inhibition of cancerous lesions |
| CZ301911B6 (cs) | 1997-11-12 | 2010-07-28 | Bayer Schering Pharma Aktiengesellschaft | 2-Fenylsubstituované imidazotriazinony, zpusob jejich výroby, léciva tyto látky obsahující a jejich použití |
| US5852035A (en) * | 1997-12-12 | 1998-12-22 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to substituted N- arylmethyl and heterocyclmethyl-1H-pyrazolo (3,4-B) quinolin-4-amines |
| US6410584B1 (en) * | 1998-01-14 | 2002-06-25 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells with indole derivatives |
| US6046199A (en) * | 1998-01-14 | 2000-04-04 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with tetracyclic pyrido[3,4-B]indole derivatives |
| US5942520A (en) * | 1998-01-27 | 1999-08-24 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells by exposure to substituted N-cycloalkylmethyl-1-H-pyrazolo (3,4-B) quinolone-4 amines |
| US5990117A (en) * | 1998-04-15 | 1999-11-23 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to quinazoline derivatives |
| US6180629B1 (en) | 1998-08-14 | 2001-01-30 | Cell Pathways, Inc. | [4,5]-Fused-1,3-disubstituted-1,2-diazine-6-one derivatives with nitrogen containing substitutents in position one for the treatment of neoplasia |
| US6268372B1 (en) | 1998-09-11 | 2001-07-31 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,9-disubstituted purin-6-ones |
| US6124303A (en) * | 1998-09-11 | 2000-09-26 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 9-substituted 2-(2-N-aloxyphenyl) purin-6-ones |
| CA2346350C (en) * | 1998-10-05 | 2008-01-08 | Eisai Co., Ltd. | Intraoral quickly disintegrating tablets |
| US6130053A (en) * | 1999-08-03 | 2000-10-10 | Cell Pathways, Inc. | Method for selecting compounds for inhibition of neoplastic lesions |
| US6200771B1 (en) | 1998-10-15 | 2001-03-13 | Cell Pathways, Inc. | Method of using a novel phosphodiesterase in pharmaceutical screeing to identify compounds for treatment of neoplasia |
| US6133271A (en) * | 1998-11-19 | 2000-10-17 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure thienopyrimidine derivatives |
| US6187779B1 (en) | 1998-11-20 | 2001-02-13 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,8-disubstituted quinazoline derivatives |
| US6369092B1 (en) | 1998-11-23 | 2002-04-09 | Cell Pathways, Inc. | Method for treating neoplasia by exposure to substituted benzimidazole derivatives |
| US6486155B1 (en) | 1998-11-24 | 2002-11-26 | Cell Pathways Inc | Method of inhibiting neoplastic cells with isoquinoline derivatives |
| US6034099A (en) * | 1998-11-24 | 2000-03-07 | Cell Pathways, Inc. | Method for inhibiting neoplastic lesions by administering 4-(arylmethylene)- 2, 3- dihydro-pyrazol-3-ones |
| US6077842A (en) * | 1998-11-24 | 2000-06-20 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with pyrazolopyridylpyridazinone derivatives |
| US6025394A (en) | 1999-01-29 | 2000-02-15 | Cell Pathways, Inc. | Method for treating patients with acne by administering substituted sulfonyl indenyl acetic acids, amides and alcohols |
| US6020379A (en) * | 1999-02-19 | 2000-02-01 | Cell Pathways, Inc. | Position 7 substituted indenyl-3-acetic acid derivatives and amides thereof for the treatment of neoplasia |
| GB9924020D0 (en) | 1999-10-11 | 1999-12-15 | Pfizer Ltd | Pharmaceutically active compounds |
| US6555547B1 (en) | 2000-02-28 | 2003-04-29 | Cell Pathways, Inc. | Method for treating a patient with neoplasia by treatment with a vinca alkaloid derivative |
| US6569638B1 (en) | 2000-03-03 | 2003-05-27 | Cell Pathways, Inc | Method for screening compounds for the treatment of neoplasia |
| EP1392314B1 (de) * | 2001-05-09 | 2006-12-20 | Bayer HealthCare AG | NEUE VERWENDUNG VON 2-[2-Ethoxy-5-(4-methyl-piperazin-1-sulfonyl)-phenyl]-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-on |
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| US7342884B2 (en) * | 2002-03-13 | 2008-03-11 | Harmonic, Inc. | Method and apparatus for one directional communications in bidirectional communications channel |
| US7276529B2 (en) * | 2002-03-20 | 2007-10-02 | Celgene Corporation | Methods of the treatment or prevention of exercise-induced asthma using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione |
| US7893101B2 (en) | 2002-03-20 | 2011-02-22 | Celgene Corporation | Solid forms comprising (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, compositions thereof, and uses thereof |
| US7208516B2 (en) * | 2002-03-20 | 2007-04-24 | Celgene Corporation | Methods of the treatment of psoriatic arthritis using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione |
| US6962940B2 (en) | 2002-03-20 | 2005-11-08 | Celgene Corporation | (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione: methods of using and compositions thereof |
| AU2003237078C1 (en) * | 2002-04-12 | 2009-10-08 | Celgene Corporation | Methods for identification of modulators of angiogenesis, compounds discovered thereby, and methods of treatment using the compounds |
| US20050118715A1 (en) * | 2002-04-12 | 2005-06-02 | Hariri Robert J. | Modulation of stem and progenitor cell differentiation, assays, and uses thereof |
| DE10232113A1 (de) * | 2002-07-16 | 2004-01-29 | Bayer Ag | Vardenafil Hydrochlorid Trihydrat enthaltende Arzneimittel |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| DE102005001989A1 (de) * | 2005-01-15 | 2006-07-20 | Bayer Healthcare Ag | Intravenöse Formulierungen von PDE-Inhibitoren |
| DE102005009241A1 (de) * | 2005-03-01 | 2006-09-07 | Bayer Healthcare Ag | Arzneiformen mit kontrollierter Bioverfügbarkeit |
| DE102005009240A1 (de) * | 2005-03-01 | 2006-09-07 | Bayer Healthcare Ag | Arzneiformen mit verbesserten pharmakokinetischen Eigenschaften |
| WO2007039075A2 (en) * | 2005-09-29 | 2007-04-12 | Bayer Healthcare Ag | Pde inhibitors and combinations thereof for the treatment of urological disorders |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| US7879802B2 (en) | 2007-06-04 | 2011-02-01 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| WO2008151734A1 (en) * | 2007-06-13 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | Pde inhibitors for the treatment of hearing impairment |
| MX2010010334A (es) * | 2008-03-24 | 2010-10-08 | Celgene Corp | Tratamiento de psoriasis o artritis psoriatica utilizando ciclopropil-n-{2-{(1s)-1-(3-etoxi-4-metoxifenil)-2-(metilsulfonil )etil]-3-oxoisoindolina-4-il}carboxamida. |
| ES2522968T3 (es) | 2008-06-04 | 2014-11-19 | Synergy Pharmaceuticals Inc. | Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| US20110190192A1 (en) * | 2009-12-15 | 2011-08-04 | Cebix Inc. | Methods for treating erectile dysfunction in patients with insulin-dependent diabetes |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| MX357121B (es) | 2011-03-01 | 2018-06-27 | Synergy Pharmaceuticals Inc Star | Proceso de preparacion de agonistas c de guanilato ciclasa. |
| WO2014131024A2 (en) | 2013-02-25 | 2014-08-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| EP2968439A2 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| EP3004138B1 (en) | 2013-06-05 | 2024-03-13 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| KR102456567B1 (ko) | 2013-08-09 | 2022-10-19 | 알데릭스, 인코포레이티드 | 인산염 수송을 억제하기 위한 화합물 및 방법 |
| MX2016014384A (es) | 2014-06-23 | 2017-01-20 | Celgene Corp | Apremilast para el tratamiento de una enfermedad del higado o una anormalidad en la funcion del higado. |
| US20200368223A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Methods for inhibiting phosphate transport |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1425603A (fr) * | 1964-01-18 | 1966-01-24 | Kyowa Hakko Kogyo Kk | Procédé de préparation de dérivés de la purine |
| DE1545574A1 (de) * | 1964-12-14 | 1969-07-31 | Ajinomoto Kk | Verfahren zur Herstellung von Hypoxanthin und dessen Derivaten |
| GB1493685A (en) * | 1970-12-15 | 1977-11-30 | May & Baker Ltd | 8-azapurinones |
| US3819631A (en) * | 1970-12-15 | 1974-06-25 | May & Baker Ltd | Azapurinones |
| GB1338235A (en) * | 1970-12-15 | 1973-11-21 | May & Baker Ltd | Azapurinones |
| DE3131365A1 (de) * | 1981-08-07 | 1983-02-24 | Henkel KGaA, 4000 Düsseldorf | Neue diglycidyl-substituierte heterocyclische verbindungen, verfahren zu ihrer herstellung und ihre verwendung in arzneimittelzubereitungen mit cytostatischer wirksamkeit |
| US4565875A (en) * | 1984-06-27 | 1986-01-21 | Fmc Corporation | Imidazole plant growth regulators |
-
1988
- 1988-01-26 CA CA000557327A patent/CA1303037C/en not_active Expired - Fee Related
- 1988-01-27 DK DK040788A patent/DK40788A/da not_active Application Discontinuation
- 1988-01-27 EP EP88300696A patent/EP0293063B1/en not_active Expired
- 1988-01-27 US US07/148,791 patent/US4885301A/en not_active Expired - Fee Related
- 1988-01-27 IE IE880213A patent/IE880213L/xx unknown
- 1988-01-27 ES ES198888300696T patent/ES2033423T3/es not_active Expired - Lifetime
- 1988-01-27 DE DE8888300696T patent/DE3869205D1/de not_active Expired - Lifetime
- 1988-01-28 PT PT86651A patent/PT86651B/pt not_active IP Right Cessation
- 1988-01-29 AU AU10956/88A patent/AU599452B2/en not_active Ceased
-
1992
- 1992-03-04 GR GR920400382T patent/GR3003956T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT86651A (pt) | 1988-02-01 |
| AU599452B2 (en) | 1990-07-19 |
| IE880213L (en) | 1988-08-02 |
| EP0293063B1 (en) | 1992-03-18 |
| AU1095688A (en) | 1988-08-04 |
| DK40788A (da) | 1988-08-03 |
| GR3003956T3 (enrdf_load_stackoverflow) | 1993-03-16 |
| DE3869205D1 (de) | 1992-04-23 |
| EP0293063A1 (en) | 1988-11-30 |
| DK40788D0 (da) | 1988-01-27 |
| ES2033423T3 (es) | 1993-03-16 |
| PT86651B (pt) | 1992-02-28 |
| US4885301A (en) | 1989-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |